The group reportedly used secret passwords and unmarked rooms to keep their extra-curricular activities on the down low -- playing behind closed doors manned with armed guards in bullet proof vests. Members would often meet for games at the Beverly Hills hotel or the Viper Room on Sunset Boulevard -- details learned after the FBI investigation into CEO of Ruderman Capital Partners, Brad Ruderman, whose loss of $25 million of investor cash led officials to the Tinseltown 12 plus gamblers. Ruderman, is currently serving time in a Texas jail until 2018.

The multi-million dollar ring reportedly landed Maguire -- who is under a bit more water than the rest of his pals -- $300,000 over the span of several games. Only problem was that his winnings came at the expense of hedge fund manager, Ruderman, who dipped his hand in his investors' cookie jar to buy-in (buy-ins generally started at $100,000) and allegedly created a Ponzi scheme to pay off his debts.

Ruderman's clients are now going after those that won what was supposed to be their investment capital. From just trying to blow off some steam to being the only man left standing after the fog cleared from Ruderman's smoking gun accounting, Maguire could be looking at some major losses if he is forced to give up his dirty money winnings.

Although DiCaprio, Affleck and Damon were involved in the poker ring, they are not yet the target of any of these civil suits. According to a fellow player, "Matt never won" and "Leo is a tight ass. When he lost $50,000 the look in his eyes was obvious, he was crazy."

In documents filed against Maguire in LA's Bankruptcy Court, the underground gambling meetings were "exclusive events, by invitation only ... there was a regular roster of players consisting of wealthy celebrities, entrepreneurs, attorneys and businessmen."

Maguire was described as a "very, very frequent player" in the exclusive gambling ring which ran from 2006 to 2009 and reportedly won close to $1 million per month during the three year span -- translating to potentially more than $36 million.

Although, at this point, Maguire is only involved in civil suits, it is illegal to gamble for money at unspecified gambling establishments in California -- although the law is generally not strictly enforced. Maguire is not under any criminal investigation at this time.

According to the civil suit, Maguire is "not entitled to receive the transfer funds from the Debtor, which transfers were comprised of improperly diverted investor funds." But Maguire, who has hired a lawyer, will argue that his poker face winnings are not of the illegal variety.

Although Maguire's involvement doesn't bode well, for Hollywood's other gambling guys, it can only add to their method acting repertoire.

Toby McGuire should not be held accountable for the loss of the investors money, the man in jail serving time, is the person they need to retrieve their funds from, oh wait! They can't because they gave him their money and he lost it gambling at cards, if they lost it on Wall Street, would they hold they sue Wall Street, no! They would cut their losses and file their taxes and get on with their lives. IN this case, they are just trying to make others pay for this investing idiots theft of their funds. They had no idea he was using their money to play his poker hands. They don't sit at the door and ask you where you got the money, you just have to have it to buy in and your poker hands. If they hold Toby McGuire account for the loss of their persons investments, then I should be able to sue the government over the loss of the housing industry, after all the funds being used are the countries, I am part of the country, please, take Mr. McGuire, after all, if you use this as a premise to stand on, I will try it against the government for my funds lost, after all I worked and paid into the SS, medicare, taxes, you name it, the government owes me big time and with interest too. Bring it on attorney's don't think I won't try it! If they can, so can we. The investors who lost their funds through the idiot they hired to increase their money, grow up, it happens, you picked the wrong man to handle your money. You didn't do your homework, research before you hand your funds to a stranger, if you didn't get more than two dozen thumbs up on your money manager, then you didn't do your homework. Toby McGuire shouldn't have to pay anyone back. He didn't know this man was using money that was not his. As for the IRS, pay the money owed Actors for your earnings at the table and learn from this mistake. We all make mistakes, part of life, move on, don't regret, just learn.

Remember when teachers, public employees, Planned Parenthood, NPR and PBS crashed the stock market, wiped out half of our 401Ks, took trillions in TARP money, spilled oil in the Gulf of Mexico, gave themselves billions in bonuses, and paid no taxes? .....yeah, me neither. :/

But there’s a lot that’s similar about gambling and substance abuse, too. People can lose jobs and money as a result of gambling as they can with the other activities. Just as there are numerous addictive drugs, there are also many ways to engage in gambling, from casino games and slot machines, to monthly poker games, to lottery tickets. And then there’s horse racing and jail-alai and the office football pool. Internet gambling has exacerbated the problem. Russian Translation